Heterocyclically substituted phenoxysulfonylureas, and the use thereof as herbicides or plant growth regulators

ABSTRACT

Heterocyclically substituted phenoxysulfonylureas, processes for the preparation thereof, and the use thereof as herbicides or plant growth regulators. Compounds of the formula I or the salts thereof ##STR1## where R 1  is (C 1  -C 8 )alkyl, (C 2  -C 8 )alkenyl or (C 2  -C 8 )alkynyl, these radicals being substituted by halogen, saturated or unsaturated (C 1  -C 6 )alkoxy, (C 1  -C 6 )alkylthio, -sulfinyl or -sulfonyl, (C 1  -C 6 )alkoxycarbonyl, NO 2 , CN or phenyl; furthermore is (C 2  -C 8 )alkenyl, (C 2  -C 8 )alkynyl or (C 3  -C 8 )cycloalkyl, which can be substituted by halogen or by alkoxy or alkylthio; (C 5  -C 8 )cycloalkenyl, cyclopropylmethyl, epoxypropyl; furfuryl, tetrahydrofurfuryl or phenoxy (C 1  -C 4 )alkyl, it being possible for the last three substituents mentioned to be substituted by halogen, alkyl or alkoxy; or phenyl which can be substituted by halogen, alkyl, alkoxy, NO 2 , CF 3 , CN or OCHF 2  ; or, in the event that R 2  is alkenyl, alkynyl, phenyl or phenoxy, each of which can be substituted as indicated below, alkylsulfonyl or alkylsulfinyl and n≠, R 1  is also (C 1  -C 8 )alkyl, 
     R 2  radicals independently of one another are (C 1  -C 8 )-alkyl, (C 2  -C 8 )alkenyl, (C 2  -C 8 )alkynyl, phenyl, phenoxy, (C 1  -C 4 )alkoxy, (C 1  -C 4 )alkylthio, (C 1  -C 4 )-alkoxycarbonyl, (C 2  -C 4 )alkenyloxycarbonyl, (C 2  - C 4 )alkynyloxycarbonyl, it being possible for all the abovementioned radicals to be substituted by halogen, (C 1  -C 4 )alkoxy or (C 1  -C 4 )alkylthio; furthermore halogen, NO 2 , (C 1  -C 4 )alkylsulfonyl or (C 1  -C 4 )alkylsulfinyl; 
     n is 0, 1, 2 or 3; y is O or S; 
     R 3  is hydrogen, (C 1  -C 8 )alkyl, (C 2  -C 8 )alkenyl, (C 3  -C 8 )-alkynyl or (C 1  -C 4 )alkoxy; 
     R 4  is a heterocyclic radical of the formulae ##STR2## E is CH or N, G is O or CH 2 , 
     R 5  and R 6  are hydrogen, halogen, alkyl, alkoxy or alkylthio, it being possible for the abovementioned alkyl-containing radicals to be substituted by halogen, alkoxy or alkylthio, furthermore a radical of the formula --NR 12  R 13 , --OCHR 7  --CO 2  R 12 , cycloalkyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy, 
     R 7  is hydrogen or alkyl; R 8  is alkyl, --CHF 2  or --CH 2  CF; 
     R 9  and R 10  are hydrogen, alkyl, alkoxy or halogen, R 11  is hydrogen, alkyl, --CHF 2  or CH 2  CF 3 , and R 12  and R 13  are hydrogen, alkyl, alkenyl or alkynyl, have outstanding herbicidal and plant growth-regulating properties.

It is known that heterocyclically substituted phenoxysulfonylureaspossess herbicidal and plant-growth regulating properties (EP-A 4,163,EP-A 113,956, DE-A 3,151-450).

It has now been found that heterocyclically substituted sulfamic acidphenyl esters, the phenyl ester moiety of which is formed by specificpyrocatechol monoethers, are particularly suitable as herbicides andplant growth regulators.

The present invention therefore relates to compounds of the formula (I)or salts thereof ##STR3## where R¹ is (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl,(C₂ -C₈)alkynyl, each of these radicals being monosubstituted orpolysubstituted by halogen or monosubstituted or disubstituted by (C₁-C₆)alkoxy, (C₂ -C₆)alkenyloxy, (C₂ -C₆)-alkynyloxy, (C₁ -C₆)alkylthio,(C₁ -C₆)alkylsulfinyl, (C₁ -C₆)alkylsulfonyl, (C₁ -C₆)alkoxycarbonyl,NO₂, CN or by phenyl; furthermore (C₂ -C₈)alkenyl, (C₂ -C₈)-alkynyl, (C₃-C₈)cycloalkyl, which can be monosubstituted or polysubstituted byhalogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁-C₄)alkylthio; (C₅ -C₈)cycloalkenyl, cyclopropylmethyl, epoxypropyl;furfuryl, tetrahydrofurfuryl, phenoxy (C₁ -C₄)alkyl, it being possiblefor the last three substituents mentioned to be substituted by halogen,(C₁ -C₄)alkyl or (C₁ -C₄)alkoxy; or phenyl which can be monosubstitutedor polysubstituted by halogen, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, NO₂, CF₃,CN or OCHF₂ ; or in the event that R² is (C₂ -C₈)alkenyl, (C₂-C₈)-alkynyl, phenyl, phenoxy, each of which can be substituted asindicated below, (C₁ -C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl and n≠0,R¹ is also (C₁ -C₈)alkyl,

R² radicals independently of one another are (C₁ -C₈)-alkyl, (C₂-C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl, phenoxy, (C₁ -C₄)alkoxy, (C₁-C₄)alkylthio, (C₁ -C₄)alkoxycarbonyl, (C₂ -C₄)alkenyloxycarbonyl or (C₂-C₄)alkynyloxycarbonyl, it being possible for all of the abovementionedradicals to be monosubstituted or polysubstituted by halogen ormonosubstituted to disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio;furthermore are halogen, NO₂, (C₁ -C₄)alkylsulfonyl or (C₁-C₄)alkylsulfinyl;

n is 0, 1, 2 or 3;

Y is O or S;

R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₃ -C₈)-alkynyl or (C₁-C₄)alkoxy;

R⁴ is a heterocyclic radical of the formulae ##STR4## E is CH or N, G isO or CH₂,

R⁵ and R⁶ independently of one another are hydrogen, halogen, (C₁ -C₆)alkyl, (C₁ -C₆) alkoxy or (C₁ -C₆) alkylthio, it being possible for theabovementioned alkyl-containing radicals to be monosubstituted orpolysubstituted by halogen or monosubstituted or disubstituted by (C₁-C₄) alkoxy or (C₁ -C₄)alkylthio, furthermore are a radical of theformula --NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃ -C₆)cycloalkyl, (C₃-C₅)alkenyl, (C₂ -C₄)alkynyl, (C₃ -C₅)alkenyloxy, or (C₃ -C₅)alkynyloxy,

R⁷ is hydrogen or (C₁ -C₄)alkyl,

R⁸ is (C₁ -C₄)alkyl, --CHF₂ or --CH₂ CF₃,

R⁹ and R¹⁰ independently of one another are hydrogen, (C₁ -C₄)alkyl, (C₁-C₅)alkoxy or halogen,

R¹¹ is hydrogen, (C₁ -C₄)alkyl, -CHF₂ or CH₂ CF₃ and

R¹² and R¹³ independently of one another are hydrogen, (C₁ -C₄)alkyl,(C₂ -C₄)alkenyl or (C₃ -C₄)alkynyl.

The compounds of the formula (I) can form salts in which the hydrogen ofthe -SO₂ -NH- group is replaced by a cation which is suitable foragriculture. In general, these salts are metal salts, in particularalkali metal salts, alkaline earth metal salts, optionally alkylatedammonium salts or organic amine salts.

Preferred compounds of the formula (I) and salts thereof are those inwhich R¹ is (C₁ -C₄)alkyl, (C₂ -C₅)alkenyl or (C₂ -C₄)alkynyl, theseradicals being substituted as described above; furthermore is (C₂-C₅)alkenyl, (C₂ -C₄)alkynyl or, in the event that n=1 and R² is (C₂-C₈)alkenyl or (C₂ -C₈)alkynyl, is (C₁ -C₄)alkyl; R² is (C₁ -C₄)alkyl,(C₂ -C₅)alkenyl, (C₂ -C₄)alkynyl, (C₁ -C₄)alkoxycarbonyl, phenyl,phenoxy, (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio, it being possible forthese radicals to be substituted as described above; or is halogen; n is0, 1 or 2, Y is O, R³ is hydrogen, (C₁ -C₄)alkyl or (C₃ -C₄)alkenyl, R⁴is a heterocyclic radical of the formula ##STR5## E is CH or N, R⁵ andR⁶ independently of one another are halogen, (C₁ -C₄)alkyl, (C₁-C₄)alkoxy or (C₁ -C₄)alkylthio, each of which can be substituted asdescribed above.

Halogen is preferably fluorine, chlorine or bromine.

Particularly preferred compounds of the formula (I) and salts thereofare those where R¹ is (C₁ -C₄)alkyl, (C₂ -C₅)alkenyl or (C₂ -C₄)alkynyl,these radicals being substituted as described above, furthermore (C₂-C₅)alkenyl or (C₂ -C₄)alkynyl; R² is (C₁ -C₄)alkyl, (C₂ -C₅)alkenyl,(C₁ -C₄)alkoxycarbonyl, (C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio, each of whichcan be substituted as described above; or is fluorine or chlorine, n=0or 1, R³ is hydrogen or methyl, R⁴ is a heterocyclic radical of theformula ##STR6## E is CH or N and R⁵ and R⁶ independently of one anotherare chlorine, bromine, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, OCHF₂, OCH₂ CF₃ orCF₃.

The present invention also relates to processes for the preparation ofcompounds of the general formula (I) or salts thereof, characterized inthat

(a) a compound of the formula (II) ##STR7## is reacted with a compoundof the formula (III) ##STR8## or (b) a compound of the formula (IV)##STR9## is reacted with a chlorosulfonylurea of the formula (V)##STR10## or (c) a compound of the formula (VI) ##STR11## is reactedwith a carbamate of the formula (VII) ##STR12## where Z is phenyl or (C₁-C₆)alkyl, and, if desired, the resulting compounds of the formula I areconverted into their salts.

The compounds of the formulae (II) and (III) are preferably reacted ininert aprotic solvents, such as, for example, acetonitrile,dichloromethane, toluene, tetrahydrofuran or dioxane, at temperaturesbetween 0° C. and the boiling point of the solvent.

The phenoxysulfonyl isocyanates of the formula (II) can be prepared in asimple manner by processes which are known in principle from thecorresponding pyrocatechol monoethers of the formula (IV) andchlorosulfonyl isocyanate (cf. G. Lohaus, Chem. Ber. 105, 2791 (1972)).

The starting substances of the formula (III) are known or can beprepared by processes which are known in principle, for example bycyclizing corresponding guanidine derivatives with appropriatelysubstituted 1,3-diketones, cf., for example, "The Chemistry ofHeterocyclic Compounds", Vol. XVI (1962) and Supplement I (1970), or byderivatization of cyanuric chloride, cf., for example, "The Chemistry ofHeterocyclic Compounds", L. Rapaport: "s-Triazines and Derivatives"(1959).

The reaction of the compounds (IV) with the chlorosulfonylureas (V) ispreferably carried out in inert solvents, such as, for example,dichloromethane, at temperatures between -10° C. and 80° C. in thepresence of a base as the HCl-binding agent. Bases which can be employedare alkali metal carbonates, alkali metal bicarbonates, alkaline earthmetal carbonates or alkaline earth metal bicarbonates, such as, forexample, K₂ CO₃, NaHCO₃, Na₂ CO₃, or tertiary amines, such as, forexample, pyridine or triethylamine.

The pyrocatechol monothers (IV) are known from the literature or can beprepared by processes which are known from the literature. Thechlorosulfonylureas (V) are accessible from the amines of the formula(III) and chlorosulfonyl isocyanate (EP-A 141,199).

The reaction of the compounds (VI) with the heterocyclic carbamates ofthe formula VII is preferably carried out in the presence of tertiaryorganic bases, such as, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU), in inert solvents, such as acetonitrile or dioxane, attemperatures between 20° C. and the boiling point of the solvent(analogously to EP-A 44,807).

The carbamates (VII), which are required for this process, are knownfrom the literature or are prepared by known processes (EP-A 70,804).The sulfamates (VI) are prepared from the pyrocatechol monoethers onwhich they are based by known processes (cf., for example, Synthesis1978, 357; Z. Chem. 15, 270 (1975); Chem. Ber. 105, 2791 (1972)).

The salts of the compounds of the formula I are preferably prepared ininert solvents, such as, for example, water, methanol or acetone, attemperatures from 0°-100° C. Examples of bases which are suitable forthe preparation of the salts according to the invention are alkali metalcarbonates, such as potassium carbonate, alkali metal hydroxides andalkaline earth metal hydroxides, ammonia or ethanolamine.

The compounds of the formula I according to the invention have anexcellent herbicidal activity against a broad range of economicallyimportant monocotyledon and dicotyledon noxious plants. The activesubstances act equally well on perennial weeds which produce shoots fromrhizomes, rootstocks or other perennial organs and which cannot beeasily controlled. In this context, it does not matter if the substancesare applied before sowing, as a pre-emergence treatment orpost-emergence treatment. Some representatives of the monocotyledon anddicotyledon weed flora which can be controlled may be mentionedindividually as examples, but this is not to be taken to mean arestriction to certain species.

The monocotyledon weed species controlled include, for example, Avena,Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria etc. andCyperus species from the annual group, and the perennial species includeAgropyron, Cynodon, Imperata and Sorghum etc., and also perennialCyperus species.

Of the dicotyledon weed species, the range of action covers species suchas, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus,Sinapis, Ipomoea, Matricaria, Abutilon, Sida etc. from the annualplants, and Convolvulus, Cirsium, Rumex, Artemisia etc. from theperennials.

Excellent control of weeds occurring under the specific cultureconditions in rice, such as, for example, Sagittaria, Alisma,Eleocharis, Scirpus, Cyperus etc., by the active substances according tothe invention is also possible.

If the compounds according to the invention are applied to the soilsurface before germination, either emergence of the weed seedlings isprevented completely, or the weeds grow until they have reached thecotyledon stage but growth then comes to a standstill and, after aperiod of three to four weeks, the plants eventually die completely.When, in the post-emergence method, the active substances are applied tothe green parts of the plants, growth also stops dramatically very soonafter the treatment, and the weed plants remain in the growth stage ofthe time of application, or, after a certain period of time, die more orless rapidly, so that competition by the weeds, which is detrimental forthe crop plants, can thus be prevented at a very early stage and in asustained manner by using the novel agents according to the invention.

Even though the compounds according to the invention have an excellentherbicidal activity against monocotyledon and dicotyledon weeds, cropplants of economically important crops such as, for example, wheat,barley, rye, rice, maize, sugar beet, cotton and soya beans, are damagedonly to a negligible extent, or not at all. Thus, the present compoundsare very suitable for selectively controlling undesired plant growth inagricultural plantations of useful plants.

In addition, the compounds according to the invention have plantgrowth-regulating properties in crop plants. They have a regulatingeffect on the plant metabolism and can thus be employed for facilitatingharvesting, such as, for example, by provoking desiccation, abscissionand stunted growth. Furthermore, they are suitable for generallyregulating and inhibiting undesired vegetative growth, withoutsimultaneously destroying the plants. Inhibition of vegetative growthplays an important role in many monocotyledon and dicotyledon cropsbecause lodging can be reduced hereby, or prevented completely.

The agents according to the invention can be employed in theconventional preparations as wettable powders, emulsifiableconcentrates, emulsions, sprayable solutions, dusting agents,seed-dressing agents, dispersions, granules or microgranules.

Wettable powders are preparations which are uniformly dispersible inwater and which, besides the active substance, also contain wettingagents, for example, polyoxyethylated alkylphenols, polyoxyethylatedfatty alcohols, alkylsulfonates or alkylphenylsulfonates, and dispersingagents, for example, sodium ligninsulfonate, sodium2,2'-dinaphthylmethane-6,6'-disulfonate, sodiumdibutylnaphthalenesulfonate and also sodium oleoylmethyltaurinate, aswell as, if appropriate, a diluent or inert substance. The formulationsare prepared in a customary manner, for example by grinding and mixingof the components.

Emulsifiable concentrates can be prepared, for example, by dissolvingthe active substances in an inert organic solvent, for example butanol,cyclohexanone, dimethylformamide, xylene and also higher-boilingaromatics or hydrocarbons, with the addition of one or more emulsifiers.In the case of liquid active substances, all or part of the solventcomponent can be omitted. Emulsifiers which can be used are, forexample: calcium salts of alkylarylsulfonic acid, such as Cadodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide/ethylene oxide condensation products, fattyalcohol/propylene oxide/-ethylene oxide condensation products, alkylpolyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitanfatty acid esters or polyoxyethylene sorbitol esters.

Dusting agents are obtained by grinding the active substance with finelydivided solid substances, for example talc or natural clays, such askaolin, bentonite, pyrophillite, or diatomaceous earth.

Granules can be produced either by spraying the active substance ontoadsorptive, granulated inert material or by applying active substanceconcentrates onto the surface of carriers such as sand, kaolinites orgranulated inert material, by means of binders, for example polyvinylalcohol, sodium polyacrylate or alternatively mineral oils. Suitableactive substances can also be granulated in the manner which isconventional for the preparation of fertilizer granules, if desired in amixture with fertilizers.

The active substance concentration in wettable powders is, for example,about 10 to 90% by weight; the remainder to 100% by weight comprisesconventional formulation components. In the case of emulsifiableconcentrates, the active substance concentration can be about 5 to 80%by weight. Formulations in the form of dusts usually contain 5 to 20% byweight, sprayable solutions about 2 to 20% by weight. In the case ofgranules, the active substance content depends partly on whether theactive compound is liquid or solid and on which granulation auxiliaries,fillers etc. are used.

In addition, the active substance formulations mentioned contain, ifappropriate, the adhesives, wetting agents, dispersing agents,emulsifiers, penetrants, solvents, fillers or carriers which areconventional in each case.

For use, the concentrates, present in commercially available form, arediluted, if appropriate, in a conventional manner, for example usingwater in the case of wettable powders, emulsifiable concentrates,dispersions and, in some cases, also in the case of microgranules.Preparations in the form of dusts and in the form of granules and alsosprayable solutions are usually not further diluted with other inertsubstances before use.

The application rate required varies with the external conditions, suchas temperature, humidity amongst others. It can vary within wide limits,for example between 0.005 and 10.0 kg/ha or more of active substance,preferably, however, it is between 0.01 and 5 kg/ha.

If appropriate, mixtures or mixed formulations with other activesubstances, such as, for example, insecticides, acaricides, herbicides,fertilizers, growth regulators or fungicides are also possible.

The following examples illustrate the invention in greater detail.

FORMULATION EXAMPLES

A. A dusting agent is obtained by mixing 10 parts by weight of activesubstance and 90 parts by weight of talc or inert substance, andcomminuting the mixture in a hammer mill.

B. A wettable powder which is readily dispersible in water is obtainedby mixing 25 parts by weight of active substance, 64 parts by weight ofkaolin-containing quartz as inert substance, 10 parts by weight ofpotassium ligninsulfonate and 1 part by weight of sodiumoleoylmethyltaurinate as wetting and dispersing agent, and grinding themixture in a pinned disk mill.

C. A dispersion concentrate which is readily dispersible in water isobtained by mixing 20 parts by weight of active substance with 6 partsby weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts byweight of isotridecanol polyglycol ether (8 EO) and 71 parts by weightof paraffinic mineral oil (boiling range, for example, about 255° toabove 377° C.), and grinding the mixture in a ball mill to a fineness ofbelow 5 microns.

D. An emulsifiable concentrate is obtained from 15 parts by weight ofactive substance, 75 parts by weight of cyclohexanone as solvent and 10parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.

CHEMICAL EXAMPLES Example 1 2-(2-Chloroethoxy)phenoxysulfonyl isocyanate

3.4 g (0.024 mol) of chlorosulfonyl isocyanate are added dropwise at 25°C. to a solution of 3.45 g (0.02 mol) of 2-(2-chloroethoxy)phenol in 20ml of xylene. When the dropwise addition is complete, the temperature isincreased slowly to 140° C., and the mixture is refluxed for 2 hours.The mixture is cooled and the solvent as well as excess chlorosulfonylisocyanate are removed on a rotary evaporator. The yellow oil whichremains (5.6 g=100% of theory) is employed without further purification.

Example 21-[2-(2-Chloroethoxy)phenoxysulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea

A solution of 5.6 g (0.02 mol) of the product of Example 1 in 20 ml ofdichloromethane is added dropwise at 0° C. to 3.1 g (0.02 mol) of2-amino-4,6-dimethoxypyrimidine in 30 ml of dichloromethane. Thereaction mixture is allowed to reach room temperature, and stirring iscontinued for 24 hours. The reaction solution is diluted using 100 ml ofdichloromethane and washed with 50 ml of 1N hydrochloric acid and 50 mlof water. The organic phase is dried using sodium sulfate, and thesolvent is removed on a rotary evaporator. The viscous oil which remainsis crystallized by trituration with diethyl ether. 7.7 g (89% of theory)of1-[2-(2-chloroethoxy)phenoxy-sulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)ureaof melting point 132°-134° C. are obtained.

Example 33-(4,6-Dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea

3.1 g (0.02 mol) of 2-amino-4,6-dimethoxypyrimidine are dissolved in 30ml of dichloromethane, and 5.1 g (0.02 mol) of2-propargyloxyphenoxysulfonyl isocyanate--dissolved in 20 ml ofdichloromethane--are added at 0° C. After the reaction mixture has beenstirred for 24 hours at room temperature, it is diluted with 50 ml ofdichloromethane, washed with 50 ml of 1N hydrochloric acid and 50 ml ofwater, dried and evaporated. The oily residue crystallizes ontrituration with diethyl ether. 7.4 g (91% of theory) of3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea ofmelting point 125°-126° C. are obtained.

Example 43-(4,6-Dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)phenoxysulfonyl]urea

1.74 g (0.0063 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamateare dissolved in 80 ml of acetonitrile, and 1.48 g (0.006 mol) of2-(2-methoxyethoxy)phenyl sulfamate are added at room temperature. 1.0 g(0.0066 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added andthe reaction mixture is then stirred at room temperature for 18 hours,concentrated, diluted with H₂ O and acidified with 2N hydrochloric acidto give a pH of 3-4. After the solids have been filtered off withsuction and dried, 2.4 g (93% of theory) of3-(4,6-dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)phenoxysulfonyl]ureaof melting point 106°-108° C. are obtained.

The compounds of the Tables which follow are prepared in an analogousmanner as described in Examples 1-4.

                                      TABLE 1                                     __________________________________________________________________________     ##STR13##                                                                    Ex. No.                                                                            R.sup.1   (R.sup.2).sub.n                                                                        R.sup.3 R.sup.5                                                                             R.sup.6                                                                              E  n m.p. [°C.]           __________________________________________________________________________     5   CH.sub.2 CH.sub.2 Cl                                                                             H       CH.sub.3                                                                            CH.sub.3                                                                             CH 0                              6   "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                              7   "                  H       CH.sub.3                                                                            CH.sub.3                                                                             N  0                              8   "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                              9   "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                              10  "                  H       OCH.sub.3                                                                           Cl     CH 0                              11  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                              12  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                              13  "                  H       OCH.sub.3                                                                           Br     CH 0                              14  "                  H       CH.sub.3                                                                            Cl     CH 0                              15  "                  H       OCH.sub.3                                                                           H      CH 0                              16  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                              17  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           N  0                              18  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           CH 0                              19  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           N  0                              20  "                  H       OCH.sub.3                                                                           SCH.sub.3                                                                            CH 0                              21  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     CH 0                              22  "                  H       OCH.sub.3                                                                           OC.sub.3 H.sub.7                                                                     CH 0                              23  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N  0                              24  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                              25  "                  H       OC.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                     CH 0                              26  "                  H       C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            CH 0                              27  "                  H       CF.sub.3                                                                            OCH.sub.3                                                                            CH 0                              28  "                  H       OCH.sub.2 CF.sub.3                                                                  CH.sub.3                                                                             CH 0                              29  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                              30  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.2 CF.sub.3                                                                   CH 0                              31  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           CH 0                              32  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                              33  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           N  0                              34  "                  H       OCH.sub.3                                                                           NHC.sub.2 H.sub.5                                                                    CH 0                              35  "                  H       OCH.sub.2 CF.sub.3                                                                  NHC.sub.2 H.sub.5                                                                    CH 0                              36  "                  H       OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                    CH 0                              37  "                  H       OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH 0                              38  CH.sub.2 CH.sub.2 OCH.sub.3                                                                      H       CH.sub.3                                                                            CH.sub.3                                                                             CH 0 103-105                      39  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                              40  "                  H       CH.sub.3                                                                            CH.sub.3                                                                             N  0                              41  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                              42  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                              43  "                  H       OCH.sub.3                                                                           Cl     CH 0 Resin                        44  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                              45  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                              46  "                  H       OCH.sub.3                                                                           Br     CH 0                              47  "                  H       CH.sub.3                                                                            Cl     CH 0                              48  "                  H       OCH.sub.3                                                                           H      CH 0                              49  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                              50  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           N  0                              51  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           CH 0                              52  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           N  0                              53  "                  H       OCH.sub.3                                                                           SCH.sub.3                                                                            CH 0                              54  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     CH 0                              55  "                  H       OCH.sub.3                                                                           OC.sub.3 H.sub.7                                                                     CH 0                              56  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N  0                              57  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                              58  "                  H       OC.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                     CH 0                              59  "                  H       C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            CH 0                              60  "                  H       CF.sub.3                                                                            OCH.sub.3                                                                            CH 0                              61  "                  H       OCH.sub.2 CF.sub.3                                                                  CH.sub.3                                                                             CH 0                              62  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                              63  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.2 CF.sub.3                                                                   CH 0                              64  CH.sub.2 CH.sub.2 OCH.sub.3                                                                      H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           CH 0                              65  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                              66  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           N  0                              67  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                              68  "                  H       OCH.sub.2 CF.sub.3                                                                  NHC.sub.2 H.sub.5                                                                    CH 0                              69  "                  H       OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                    CH 0                              70  "                  H       OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH 0                               71 CH.sub.2 CHCH.sub.2                                                                              H       CH.sub.3                                                                            CH.sub.3                                                                             CH 0 128-133                      72  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0 89-90                        73  "                  H       CH.sub.3                                                                            CH.sub.3                                                                             N  0                              74  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0 112-115                      75  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                              76  "                  H       OCH.sub.3                                                                           Cl     CH 0                              77  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                              78  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                              79  "                  H       OCH.sub.3                                                                           Br     CH 0                              80  "                  H       CH.sub.3                                                                            Cl     CH 0                              81  "                  H       OCH.sub.3                                                                           H      CH 0                              82  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                              83  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           N  0                              84  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0 123                          85  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           N  0                              86  "                  H       OCH.sub.3                                                                           SCH.sub.3                                                                            CH 0                              87  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     CH 0                              88  "                  H       OCH.sub.3                                                                           OC.sub.3 H.sub.7                                                                     CH 0                              89  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N  0                              90  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                              91  "                  H       OC.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                     CH 0                              92  "                  H       C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            CH 0                              93  "                  H       CF.sub.3                                                                            OCH.sub.3                                                                            CH 0                              94  "                  H       OCH.sub.2 CF.sub.3                                                                  CH.sub.3                                                                             CH 0                              95  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                              96  CH.sub.2 CHCH.sub.2                                                                              H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.2 CF.sub.3                                                                   CH 0                              97  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           CH 0                              98  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                              99  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           N  0                             100  "                  H       OCH.sub.3                                                                           NHC.sub.2 H.sub.5                                                                    CH 0                             101  "                  H       OCH.sub.2 CF.sub.3                                                                  NHC.sub.2 H.sub.5                                                                    CH 0                             102  "                  H       OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                    CH 0                             103  "                  H       OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH 0                             104  CH.sub.2 CCH       H       OCH.sub.3                                                                           Cl     N  0                             105  "                  H       CH.sub.3                                                                            CH.sub.3                                                                             CH 0 128-133                                                                       (decomp.)                   106  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0 143-146                     107  "                  H       CH.sub.3                                                                            CH.sub.3                                                                             N  0                             108  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             109  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             110  "                  H       OCH.sub.3                                                                           Cl     CH 0                             111  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             112  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             113  "                  H       OCH.sub.3                                                                           Br     CH 0                             114  "                  H       CH.sub.3                                                                            Cl     CH 0                             115  "                  H       OCH.sub.3                                                                           H      CH 0                             116  "                  H       OCH.sub. 3                                                                          NHCH.sub.3                                                                           CH 0                             117  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           N  0                             118  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           CH 0                             119  "                  H       CH.sub.3                                                                            NHCH.sub.3                                                                           N  0                             120  "                  H       OCH.sub.3                                                                           SCH.sub.3                                                                            CH 0                             121  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     CH 0                             122  "                  H       OCH.sub.3                                                                           OC.sub.3 H.sub.7                                                                     CH 0                             123  "                  H       OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N  0                             124  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             125  "                  H       OC.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                     CH 0                             126  "                  H       C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                            CH 0                             127  CH.sub.2 CCH       H       CF.sub.3                                                                            OCH.sub.3                                                                            CH 0                             128  "                  H       OCH.sub.2 CF.sub.3                                                                  CH.sub.3                                                                             CH 0                             129  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             130  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.2 CF.sub.3                                                                   CH 0                             131  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           CH 0                             132  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             133  "                  H       OCH.sub.2 CF.sub.3                                                                  NHCH.sub.3                                                                           N  0                             134  "                  H       OCH.sub.3                                                                           NHC.sub.2 H.sub.5                                                                    CH 0                             135  "                  H       OCH.sub.2 CF.sub.3                                                                  NHC.sub.2 H.sub.5                                                                    CH 0                             136  "                  H       OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                    CH 0                             137  "                  H       OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH 0                             138  CH.sub.2 CClCH.sub.2                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             139  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             140  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             141  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             142  "                  H       OCH.sub.3                                                                           Cl     CH 0                             143  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             144  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             145  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             146  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             147  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             148  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             149  CH.sub.2 CHCHCl    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             150  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             151  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             152  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             153  "                  H       OCH.sub.3                                                                           Cl     CH 0                             154  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             155  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             156  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             157  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             158  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             159  CH.sub.2 CHCl      H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             160  CH.sub.2 C(CH.sub.3)CH.sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             161  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             162  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             163  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             164  "                  H       OCH.sub.3                                                                           Cl     CH 0                             165  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             166  "                  H       OCF.sub.2 H                                                                         CF.sub.2 H                                                                           CH 0                             167  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             168  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             169  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             170  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             171  CH.sub.2 CHCHCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             172  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             173  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             174  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             175  "                  H       OCH.sub.3                                                                           Cl     CH 0                             176  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             177  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             178  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             179  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             180  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             181  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             182  CH.sub.2 CCCH.sub.3                                                                              H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             183  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             184  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             185  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             186  "                  H       OCH.sub.3                                                                           Cl     CH 0                             187  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             188  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             189  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             190  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             191  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             192  CH.sub.2 CCCH.sub.3                                                                              H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             193  CH.sub.2 CH.sub.2 Br                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             194  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             195  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             196  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            N  0                             197  "                  H       OCH.sub.3                                                                           Cl     CH 0                             198  "                  H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH 0                             199  "                  H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH 0                             100  "                  H       OCH.sub.3                                                                           NHCH.sub.3                                                                           CH 0                             101  "                  H       Cl    OC.sub.2 H.sub.5                                                                     CH 0                             102  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH 0                             203  "                  H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N  0                             204  CH.sub.2 CH(OCH.sub.3).sub.2                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             205  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             206  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             207  C.sub.6 H.sub.5    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0 117-119                     208  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0 138-139                     209  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0 120-122                     210  "                  H       CH.sub.3                                                                            Cl     CH 0 147-148                     211  "                  H       OCH.sub.3                                                                           Cl     CH 0                             212  "                  H       CH.sub. 3                                                                           CH.sub.3                                                                             CH 0 136-138                     213  CF.sub.2 CHFCF.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0 122-124                     214  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             215  "                  H       Cl    OCH.sub.3                                                                            CH 0 160-162                     216  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             217  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                         0 Resin                       218  CH.sub.2 C.sub.6 H.sub.5                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             219  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             220  CF.sub.2 CClFH     H       OCH.sub.3                                                                           Cl     CH 0 106-110                     221  CCH.sub.3 CHCH.sub.2                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             222  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             223  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             224  C.sub.5 H.sub.9    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0                             225  C.sub.5 H.sub.9    H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             226  CF.sub.2 CClFH     H       CH.sub.3                                                                            CH.sub.3                                                                             CH 0 63-66                       227  "                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH 0 109-110                     228  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH 0                             229  "                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N  0                             230  CH.sub.2 CHCH.sub.2                                                                     6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               231  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               232  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                233  CH.sub.2 CH.sub.2 Cl                                                                    6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               234  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               235  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                236  CH.sub.2 CCH                                                                            6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               237  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               238  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                239  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               240  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               241  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                242  CH.sub.2 C.sub.6 H.sub.5                                                                6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               243  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               244  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                245  CCH.sub.3 CHCH.sub.2                                                                    6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               246  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               247  "         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                248  C.sub.5 H.sub.9                                                                         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               249  C.sub.5 H.sub.9                                                                         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               250  C.sub.5 H.sub.9                                                                         6-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                251  CH.sub.2 CHCH.sub.2                                                                     5-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               252  CH.sub.2 CHCH.sub.2                                                                     5-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               253  CH.sub.2 CH.sub.2 Cl                                                                    5-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                254  "         5-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               255  CH.sub.2 CH.sub.2 OCH.sub.3 H                                                           5-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               256  "         5-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                257  CH.sub.2 CCH                                                                            5-CH.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               258  "         5-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               259  CH.sub.2 CH.sub.2 Br                                                                    4-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                260  "         4-CH.sub.3                                                                             H       OCH.sub. 3                                                                          OCH.sub.3                                                                            CH                               261  CH.sub.2 CCCH.sub.3                                                                     3-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               262  "         3-CH.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                263  CH.sub.2 CHCH.sub.2                                                                     6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               264  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               265  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                266  CH.sub.2 CH.sub.2 Cl                                                                    6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               267  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               268  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                269  CH.sub.2 CCH                                                                            6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               270  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               271  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                272  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               273  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               274  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                275  CH.sub.2 CCH.sub.3CH.sub.2                                                              6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               276  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               277  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                278  C.sub.6 H.sub.5                                                                         6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               279  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               280  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                281  CH.sub.2 CH(OCH.sub.3).sub.2                                                            6-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               282  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               283  "         6-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                284  CH.sub.2 CHCH.sub.2                                                                     5-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               285  "         5-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               286  CH.sub.2 CH.sub.2 Cl                                                                    4-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                287  CH.sub.2 CH.sub.2 Cl                                                                    5-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               288  CH.sub.2 CH.sub.2 OCH.sub.3                                                             5-Cl     OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                      289  "         5-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                290  CH.sub.2 CCH                                                                            5-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               291  "         5-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               292  CH.sub.2 CHCHCl                                                                         4-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                293  "         4-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               294  CH.sub.2 C.sub.6 H.sub.5                                                                3-Cl     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               295  "         3-Cl     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                296  CH.sub.2 CHCH.sub.2                                                                     6-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               297  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               298  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                299  CH.sub.2 H.sub.2 Cl                                                                     6-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               300  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               301  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                302  CH.sub.2 CCH                                                                            6-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               303  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               304  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                305  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               306  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               307  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                308  CH.sub.2 CHCHCH.sub.3                                                                   6-F      H       OCH   OCH.sub.3                                                                            CH                               309  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               310  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                311  CF.sub.2 CClFH                                                                          6-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               312  "         6-F      H       OCH.sub. 3                                                                          CH.sub.3                                                                             CH                               313  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                314  CH.sub.2 CCCH.sub.3                                                                     6-F      H       OCH   OCH    CH                               315  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               316  "         6-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                317  CH.sub.2 CHCH.sub.2                                                                     5-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               318  CH.sub.2 CHCH.sub.2                                                                     5-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               319  CH.sub.2 CH.sub.2 Cl                                                                    5-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                320  "         5-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               321  CH.sub.2 CH.sub.2 OCH.sub.3                                                             5-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               322  "         5-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                323  CH.sub.2 CCH                                                                            5-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               324  "         5-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               325  CH.sub.2 CH.sub.2 Br                                                                    4-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                326  "         4-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               327  C.sub.5 H.sub.9                                                                         3-F      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               328  C.sub.5 H.sub.9                                                                         3-F      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                329  CH.sub.2 CHCH.sub.2                                                                     6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               330  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               331  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                332  CH.sub.2 CH.sub.2 Cl                                                                    6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               333  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               334  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                335  CH.sub.2 CCH                                                                            6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               336  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               337  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                338  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               339  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               340  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                341  CH.sub.2 CHCHCH.sub.3                                                                   6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               342  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               343  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                344  CH.sub.2 CHCHCl                                                                         6-COOCH.sub. 3                                                                         H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               345  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               346  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                347  C.sub.6 H.sub.5                                                                         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               348  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               349  "         6-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                350  CH.sub.2 CHCH.sub.2                                                                     5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               351  "         5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               352  CH.sub.2 CH.sub.2 Cl                                                                    5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                353  CH.sub.2 CH.sub.2 Cl                                                                    5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               354  CH.sub.2 CH.sub.2 OCH.sub.3                                                             5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               355  "         5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                356  CH.sub.2 CCH                                                                            5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               357  "         5-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               358  CH.sub.2 CH.sub.2 Br                                                                    4-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                359  "         4-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               360  CH.sub.2 CClCH.sub.2                                                                    3-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               361  "         3-COOCH.sub.3                                                                          H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                362  CH.sub.2 CHCH.sub.2                                                                     6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               363  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               364  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                365  CH.sub.2 CH.sub.2 Cl                                                                    6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               366  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               367  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                368  CH.sub.2 CCH                                                                            6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               369  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               370  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                371  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               372  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               373  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                374  CH.sub.2 CH.sub.3                                                                       6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH   131-132                     375  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH   134-136                     376  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                377  CH(CH.sub.3).sub.2                                                                      6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               378  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               379  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                380  CH.sub.2 CH.sub.2 CH.sub.3                                                              6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               381  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               382  "         6-CH.sub.2 CHCH.sub.2                                                                  H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                383  CH.sub.2 CHCH.sub.2                                                                     6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               384  "         6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               385  CH.sub.2 CH.sub.2 Cl                                                                    6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                386  "         6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               387  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               388  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                389  CH.sub.2 CCH                                                                            6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               390  "         6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               391  CH.sub.2 CH.sub.2 Br                                                                    6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                392  "         6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               393  CH.sub.2 CClCH.sub.2                                                                    6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH    CH                               394  "         6-CH.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                395  CH.sub.2 CHCH.sub.2                                                                     6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               396  "         6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               397  CH.sub.2 CH.sub.2 Cl                                                                    6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                398  "         6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               399  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               400  "         6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                401  CH.sub.2 CCH                                                                            6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               402  "         6-OCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               403  CH.sub.2 CH.sub.2 Cl                                                                    6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                404  "         6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               405  CH.sub.2 CHCH.sub.2                                                                     6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               406  "         6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                407  CH.sub.2 CCH                                                                            6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               408  "         6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           CHHD 3 CH                               409  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                410  "         6-OC.sub.6 H.sub.5                                                                     H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               411  "         6-C.sub.6 H.sub.5                                                                      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               412  "         6-C.sub.6 H.sub.5                                                                      H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                413  CH.sub.2 CCH                                                                            6-C.sub.6 H.sub.5                                                                      H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               414  "         6-C.sub.6 H.sub.5                                                                      H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               415  CH.sub.2 CH.sub.2 Br                                                                    6-SO.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                416  "         6-SO.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               417  CH.sub.2 CClCH.sub.2                                                                    6-SO.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               418  "         6-SO.sub.2 CH.sub.3                                                                    H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                419  CH.sub.2 CHCH.sub.2                                                                     6-SOCH.sub.3                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               420  "         6-SOCH.sub.3                                                                           H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               421  CH.sub.2 CH.sub.2 Cl                                                                    6-SOCH.sub.3                                                                           H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                422  "         6-SOCH.sub.3                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               423  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-SCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               424  "         6-SCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                425  CH.sub.2 CCH                                                                            6-SCH.sub.3                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               426  "         6-SCH.sub.3                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               427  CH.sub.2 CH.sub.2 Br                                                                    6-CF.sub.3                                                                             H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                428  "         6-CF.sub.3                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               429  CH.sub.2 CClCH.sub.2                                                                    6-NO.sub.2                                                                             H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               430  CH.sub.2 CH.sub.2 Cl                                                                    4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           Cl     CH                               431  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                               432  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                433  "         3,5-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               434  CH.sub.2 CH.sub.2 OCH.sub.3                                                             4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           Cl     CH                               435  "         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               436  "         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             CH                               437  "         3,5-F.sub.2                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               438  CH.sub.2 CHCH.sub.2                                                                     4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                439  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               440  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           Cl     CH                               441  "         3,5-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               442  CH.sub.2 C CH                                                                           4,6-Cl.sub.2                                                                           H       OCF.sub.2 H                                                                         CH.sub.3                                                                             CH                               443  "         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               444  "         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                445  "         3,5-F.sub.2                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               446  C.sub.6 H.sub.5                                                                         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           Cl     CH                               447  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               448  CH.sub.2 C.sub.6 H.sub.5                                                                4,6-Cl.sub.2                                                                           H       OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH                               449  "         4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               450  CH.sub.2 CHCHCH.sub.3                                                                   4,6-F.sub.2                                                                            H       OCH.sub.3                                                                           CH.sub.3                                                                             N                                451  "         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               452  CH.sub.2 CHCHCl                                                                         4,6-Cl.sub.2                                                                           H       OCH.sub.3                                                                           Cl     CH                               453  "         4,6-(CH.sub.3).sub.2                                                                   H       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               454  "         4,6-(NO.sub.2).sub.2                                                                   H       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH                               455  CH.sub.2 CH.sub.2 Cl                                                                    H        CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               456  "         H        CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             N                                457  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           OCH.sub. 3                                                                           CH                               458  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           Cl     CH                               459  CH.sub.2 CH.sub.2 OCH.sub.3                                                             H        CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               460  "         H        CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             CH                               461  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           CH                                      462  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           CH.sub.3                                                                             N                                463  CH.sub.2 CHCH.sub.2                                                                     H        CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               464  "         H        CH.sub.3                                                                              OCH.sub.3                                                                           Cl     CH                               465  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           CH                                      466  "         H        CH.sub.2 CHCH.sub.2                                                                   OCF.sub.2 H                                                                         CH.sub.3                                                                             CH                               467  CH.sub.2 CCH                                                                            H        CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               468  "         H        CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             N                                469  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               470  "         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           Cl     CH                               471  CH.sub.2 CCCH.sub.3                                                                     H        CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               472  "         H        CH.sub.2 CHCH.sub. 2                                                                  OCF.sub.2 H                                                                         OCF.sub.2 H                                                                          CH                               473  CH.sub.2 CHCHCl                                                                         H        CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               474  "         H        CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             N                                475  C.sub.6 H.sub.5                                                                         H        C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               476  CH.sub.2 CH.sub.2 Br                                                                    H        C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                           Cl     CH                               477  CH.sub.2 CCH.sub.3CH.sub.2                                                              H        C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               478  CH.sub.2 CF.sub.3                                                                       H        C.sub.2 H.sub.5                                                                       OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            CH                               479  CH.sub.2 CCH                                                                            H        C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               480  CH.sub.2 C.sub.6 H.sub.5                                                                6-CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             N                                481  CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-OCH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               482  CH.sub.2 CHCH.sub.2                                                                     6-Cl     CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           Cl     CH                               483  CH.sub.2 CH(OCH.sub.3).sub.2                                                            6-F      CH.sub.2 CHCH.sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                            CH                               484  CH.sub.2 C CH                                                                           6-CF.sub.3                                                                             CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                  OCH.sub.3                                                                            N                                __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                         ##STR14##                                                                    Ex. No. R.sup.1       (R.sup.2).sub.n                                                                         R.sup.5                                                                              m.p.                                   ______________________________________                                        485     CH.sub.2 CHCH.sub.2                                                                         H         CH.sub.3                                      486     "             H         H                                             487     "             H         OCH.sub.3                                     488     CH.sub.2 CH.sub.2 Cl                                                                        H         OCH.sub.3                                     489     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H         OCH.sub.3                                     490     CH.sub.2 CCH  H         OCH.sub.3                                     491     CH.sub.2 C.sub.6 H.sub.5                                                                    H         OCH.sub.3                                     492     CH.sub.2 CHCHCl                                                                             H         OCH.sub.3                                     493     CH.sub.2 CHCHCH.sub.3                                                                       H         OCH.sub.3                                     494     CH.sub.2 CH.sub.2 Br                                                                        H         OCH.sub.3                                     495     CH.sub.2 CCCH.sub.3                                                                         H         OCH.sub.3                                     496     C.sub.5 H.sub.9                                                                             H         OCH.sub.3                                     497     CH.sub.2 CHCH.sub.2                                                                         6-CH.sub.3                                                                              OCH.sub.3                                     498     CH.sub.2 CH.sub.2 Cl                                                                        6-OCH.sub.3                                                                             OCH.sub.3                                     499     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 6-Cl      OCH.sub.3                                     500     CH.sub.2 CHCH.sub.2                                                                         6-CF.sub.3                                                                              OCH.sub.3                                     501     CH.sub.2 CCH  6-F       OCH.sub.3                                     502     CH.sub.2 CHCHCH.sub.3                                                                       6-OCF.sub.2 H                                                                           OCH.sub.3                                     ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR15##                                                                                                                m.p.                              Ex. No.                                                                              R.sup.1      R.sup.2  R.sup.5                                                                             G    n   [°C.]                      ______________________________________                                        503    CH.sub.2 CHCH.sub.2                                                                        H        CH.sub.3                                                                            CH.sub.2                                                                           0                                     504    "            H        H     CH.sub.2                                                                           0                                     505    "            H        OCH.sub.3                                                                           CH.sub.2                                                                           0                                     506    CH.sub.2 CH.sub.2 Cl                                                                       H        CH.sub.3                                                                            O    0                                     507    CH.sub.2 CH.sub.2 OCH.sub.3                                                                H        CH.sub.3                                                                            CH.sub.2                                                                           0                                     508    CH.sub.2 CCH H        CH.sub.3                                                                            O    0                                     509    CH.sub.2 C.sub.6 H.sub.5                                                                   H        CH.sub.3                                                                            CH.sub.2                                                                           0                                     510    CH.sub.2 CHCHCl                                                                            H        CH.sub.3                                                                            O    0                                     511    CH.sub.2 CHCCH.sub.3                                                                       H        CH.sub.3                                                                            CH.sub.2                                                                           0                                     512    CH.sub.2 CH.sub.2 Br                                                                       H        CH.sub.3                                                                            O    0                                     513    CH.sub.2 CCCH.sub.3                                                                        H        CH.sub.3                                                                            CH.sub.2                                                                           0                                     514    C.sub.5 H.sub.9                                                                            H        CH.sub.3                                                                            O    0                                     515    CH.sub.2 CHCH.sub.2                                                                        6-CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.2                                                                           1                                     516    CH.sub.2 CH.sub.2 Cl                                                                       6-OCH.sub.3                                                                            CH.sub.3                                                                            O    1                                     517    CH.sub.2 CH.sub.2 OCH.sub.3                                                                6-Cl     CH.sub.3                                                                            CH.sub.2                                                                           1                                     518    CH.sub.2 CHCH.sub.2                                                                        6-CF.sub.3                                                                             CH.sub.3                                                                            O    1                                     519    CH.sub.2 CCH 6-F      CH.sub.3                                                                            CH.sub.2                                                                           1                                     520    CH.sub.2 CHCHCH.sub.3                                                                      6-OCF.sub.2 H                                                                          CH.sub.3                                                                            O    1                                     ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR16##                                                                    Ex. No. R.sup.1       R.sup.2   R.sup.5                                                                            n    m.p.                                ______________________________________                                        521     CH.sub.2 CHCH.sub.2                                                                         H         CH.sub.3                                                                           0                                        522     "             H         H    0                                        523     "             H         OCH.sub.3                                                                          0                                        524     CH.sub.2 CH.sub.2 Cl                                                                        H         CH.sub.3                                                                           0                                        525     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H         CH.sub.3                                                                           0                                        526     CH.sub.2 CCH  H         CH.sub.3                                                                           0                                        527     CH.sub.2 C.sub.6 H.sub.5                                                                    H         CH.sub.3                                                                           0                                        528     CH.sub.2 CHCHCl                                                                             H         CH.sub.3                                                                           0                                        529     CH.sub.2 CHCHCH.sub.3                                                                       H         CH.sub.3                                                                           0                                        530     CH.sub.2 CH.sub.2 Br                                                                        H         CH.sub.3                                                                           0                                        531     CH.sub.2 C CCH.sub.3                                                                        H         CH.sub.3                                                                           0                                        532     C.sub.5 H.sub.9                                                                             H         CH.sub.3                                                                           0                                        533     CH.sub.2 CHCH.sub.2                                                                         6-CH.sub.3                                                                              CH.sub.3                                                                           1                                        534     CH.sub.2 CH.sub.2 Cl                                                                        6-OCH.sub.3                                                                             CH.sub.3                                                                           1                                        535     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 6-Cl      CH.sub.3                                                                           1                                        536     CH.sub.2 CHCH 6-F       CH.sub.3                                                                           1                                        537     CH.sub.2 CCH  6-F       CH.sub.3                                                                           1                                        538     CH.sub.2 CHCHCH.sub.3                                                                       6-OCF.sub.2 H                                                                           CH.sub.3                                                                           1                                        ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR17##                                                                    Ex. No.                                                                              R.sup.1      R.sup.2  R.sup.5                                                                             R.sup.7                                                                            n   m.p.                              ______________________________________                                        539    CH.sub.2 CHCH.sub.2                                                                        H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     540    "            H        H     CH.sub.3                                                                           0                                     541    "            H        OCH.sub.3                                                                           CH.sub.3                                                                           0                                     542    CH.sub.2 CH.sub.2 Cl                                                                       H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     543    CH.sub.2 CH.sub.2 OCH.sub.3                                                                H        CH.sub.3                                                                            H    0                                     544    CH.sub.2 CCH H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     545    CH.sub.2 C.sub.6 H.sub.5                                                                   H        CH.sub.3                                                                            H    0                                     546    CH.sub.2 CHCHCl                                                                            H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     547    CH.sub.2 CHCHCH.sub.3                                                                      H        CH.sub.3                                                                            H    0                                     548    CH.sub.2 CH.sub.2 Br                                                                       H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     549    CH.sub.2 CCCH.sub.3                                                                        H        CH.sub.3                                                                            H    0                                     550    C.sub.5 H.sub.9                                                                            H        CH.sub.3                                                                            CH.sub.3                                                                           0                                     551    CH.sub.2 CHCH.sub.2                                                                        6-CH.sub.3                                                                             CH.sub.3                                                                            H    1                                     552    CH.sub.2 CH.sub.2 Cl                                                                       6-OCH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                           1                                     553    CH.sub.2 CH.sub.2 OCH.sub.3                                                                6-Cl     CH.sub.3                                                                            H    1                                     554    CH.sub.2 CHCH.sub.2                                                                        6-CF.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           1                                     555    CH.sub.2 CCH 6-F      CH.sub.3                                                                            H    1                                     556    CH.sub.2 CHCHCH.sub.3                                                                      6-OCF.sub.2 H                                                                          CH.sub.3                                                                            CH.sub.3                                                                           1                                     ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR18##                                                                    Ex.                                                                           No.  R.sup.1      R.sup.2  R.sup.5                                                                             R.sup.6                                                                             E  n m.p.                              ______________________________________                                        557  CH.sub.2 CHCH.sub.2                                                                        H        OCH.sub.3                                                                           OCH.sub.3                                                                           CH  0                                  558  "            H        OCH.sub.3                                                                           CH.sub.3                                                                            CH  0                                  559  "            H        OCH.sub.3                                                                           CH.sub.3                                                                            N  0                                   560  CH.sub.2 CH.sub.2 Cl                                                                       H        OCH.sub.3                                                                           CH.sub.3                                                                            CH  0                                  561  CH.sub.2 CH.sub.2 OCH.sub.3                                                                H        OCH.sub.3                                                                           CH.sub.3                                                                            N  0                                   562  CH.sub.2 CCH H        OCH.sub.3                                                                           OCH.sub.3                                                                           CH  0                                  563  CH.sub.2 C.sub. 6 H.sub.5                                                                  H        OCH.sub.3                                                                           CH.sub.3                                                                            N  0                                   564  CH.sub.2 CHCHCl                                                                            H        OCH.sub.3                                                                           CH.sub.3                                                                            CH  0                                  565  CH.sub.2 CHCHCH.sub.3                                                                      H        OCH.sub.3                                                                           OCH.sub.3                                                                           N  0                                   566  CH.sub.2 CH.sub.2 Br                                                                       H        OCH.sub.3                                                                           CH.sub.3                                                                            CH  0                                  567  CH.sub.2 CCCH.sub.3                                                                        H        OCH.sub.3                                                                           CH.sub.3                                                                            N  0                                   568  C.sub.5 H.sub.9                                                                            H        OCH.sub.3                                                                           OCH.sub.3                                                                           CH  0                                  569  CH.sub.2 CHCH.sub.2                                                                        6-CH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                            N  1                                   570  CH.sub.2 CH.sub.2 Cl                                                                       6-OCH.sub.3                                                                            OCH.sub.3                                                                           CH.sub.3                                                                            CH  1                                  571  CH.sub.2 CH.sub.2 OCH.sub.3                                                                6-Cl     OCH.sub.3                                                                           OCH.sub.3                                                                           N  1                                   572  CH.sub.2 CHCH.sub.2                                                                        6-CF.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3                                                                            CH  1                                  573  CH.sub.2 CCH 6-F      OCH.sub.3                                                                           OCH.sub.3                                                                           N  1                                   574  CH.sub.2 CHCHCH.sub.3                                                                      6-OCF.sub.2 H                                                                          OCH.sub.3                                                                           CH.sub.3                                                                            CH  1                                  ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR19##                                                                    Ex. No. R.sup.1       R.sup.2   R.sup.8                                                                             n   m.p.                                ______________________________________                                        575     CH.sub.2 CHCH.sub.2                                                                         H         OCH.sub.3                                                                           0                                       576     "             H         CH.sub.3                                                                            0                                       577     "             3-Cl      CH.sub.3                                                                            0                                       578     CH.sub.2 CH.sub.2 Cl                                                                        H         CH.sub.3                                                                            0                                       579     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H         CH.sub.3                                                                            0                                       580     CH.sub.2 CCH  H         OCH.sub.3                                                                           0                                       581     CH.sub.2 CHCHCl                                                                             H         CH.sub.3                                                                            0                                       582     CH.sub.2 CHCHCl                                                                             H         CH.sub.3                                                                            0                                       583     CH.sub.2 CHCHCH.sub.3                                                                       H         OCH.sub.3                                                                           0                                       584     CH.sub.2 CH.sub.2 Br                                                                        H         CH.sub.3                                                                            0                                       585     CH.sub. 2 CCCH.sub.3                                                                        H         CH.sub.3                                                                            0                                       586     C.sub.5 H.sub.11                                                                            H         OCH.sub.3                                                                           0                                       587     CH.sub.2 CHCH.sub.2                                                                         6-CH.sub.3                                                                              CH.sub.3                                                                            1                                       588     CH.sub.2 CH.sub.2 Cl                                                                        6-OCH.sub.3                                                                             CH.sub.3                                                                            1                                       589     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 6-Cl      OCH.sub.3                                                                           1                                       590     CH.sub.2 CHCH.sub.2                                                                         6-CF.sub.3                                                                              CH.sub.3                                                                            1                                       591     CH.sub.2 CCH  6-F       OCH.sub.3                                                                           1                                       592     CH.sub.2 CHCHCH.sub.3                                                                       6-OCF.sub.2 H                                                                           CH.sub.3                                                                            1                                       ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR20##                                                                    Ex.                                                                           No.  R.sup.1      R.sup.2 R7 R.sup.8                                                                             R.sup.11 n m.p.                            ______________________________________                                        593  CH.sub.2 CHCH.sub.2                                                                        HH         OCH.sub.3                                                                           H0                                         594  "            HH         CH.sub.3                                                                            CH.sub.3 0                                 595  "            HCH.sub.3  CH.sub.3                                                                            CH.sub.3 0                                 596  CH.sub.2 CH.sub.2 Cl                                                                       HH         CH.sub.3                                                                            H0                                         597  CH.sub.2 CH.sub.2 OCH.sub.3                                                                HH         CH.sub.3                                                                            CH.sub.3 0                                 598  CH.sub.2 CCH HCH.sub.3  OCH.sub.3                                                                           CHF.sub.2 0                                599  CH.sub.2 C.sub.6 H.sub.5                                                                   HH         CH.sub.3                                                                            H0                                         600  CH.sub.2 CHCHCl                                                                            HH         CH.sub.3                                                                            CH.sub.3 0                                 601  CH.sub.2 CHCHCH.sub.3                                                                      HCH.sub.3  OCH.sub.3                                                                           CH.sub.3 0                                 602  CH.sub.2 CH.sub.2 Br                                                                       HH         CH.sub.3                                                                            H0                                         603  CH.sub.2 CCCH.sub.3                                                                        HH         CH.sub.3                                                                            CH.sub.2 CF.sub.3  0                       604  C.sub.5 H.sub.9                                                                            HCH.sub.3  OCH.sub.3                                                                           CH.sub.3 0                                 605  CH.sub.2 CHCH.sub.2                                                                        6-CH.sub.3 H                                                                             CH.sub.3                                                                            H1                                         606  CH.sub.2 CH.sub.2 Cl                                                                       6-OCH3  H  CH.sub.3                                                                            CH.sub.3 1                                 607  CH.sub.2 CH.sub.2 OCH.sub.3                                                                6-ClCH.sub.3                                                                             OCH.sub.3                                                                           CH.sub.3 1                                 608  CH.sub.2 CHCH.sub.2                                                                        6-CF.sub.3 H                                                                             CH.sub.3                                                                            H1                                         609  CH.sub.2 CCH 6-FH       OCH.sub.3                                                                           CH.sub.3 1                                 610  CH.sub.2 CHCHCH.sub.3                                                                      6-ClCH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3 1                                 ______________________________________                                    

BIOLOGICAL EXAMPLES

The damage on the weed plants and the tolerance by crop plants werescored using a key where numbers from 0 to 5 express the activity. Inthis key

0 denotes no action

1 denotes 0-20% action or damage

2 denotes 20-40% action or damage

3 denotes 40-60% action or damage

4 denotes 60-80% action or damage

5 denotes 80-100% action or damage

1. Pre-emergence action on weeds

Seeds or rhizome pieces of monocotyledon and dicotyledon weed plantswere placed in plastic pots containing sandy loam soil and covered withsoil. Various dosages of aqueous suspensions or emulsions of thecompounds according to the invention formulated as wettable powders oremulsion concentrates were then applied to the surface of the coversoil, at an application rate of water of 600-800 l/ha (converted).

After the treatment, the pots were placed in the greenhouse andmaintained at good growth conditions for the weeds. Visual scoring ofthe damage to plants or the emergence damage was carried out after theemergence of the test plants after a trial period of 3 to 4 weeks,comparing them to untreated control plants. As shown by the score datain Table 9, the compounds according to the invention have goodherbicidal pre-emergence activity against a broad range of weed grassesand broad-leaf weeds.

2. Post-emergence action on weeds

Seeds or rhizome pieces of monocotyledon and dicotyledon weeds wereplaced in plastic pots in sandy loam ground, covered with soil and grownin the greenhouse under good growth conditions. Three weeks aftersowing, the test plants were treated in the three-leaf stage.

Various dosages of the compounds according to the invention formulatedas wettable powders or emulsion concentrates were sprayed onto the greenparts of the plants, at an application rate of water of 600-800 l/ha(converted), and the action of the preparations was scored visuallyafter the test plants had remained in the greenhouse for about 3 to 4weeks under optimum growth conditions, comparing them to untreatedcontrol plants.

The agents according to the invention exhibit a good herbicidal activityagainst a broad range of economically important weed grasses andbroad-leaf weeds, also in the post-emergence treatment (Table 10).

3. Tolerance by crop plants

In further greenhouse experiments, seeds of a relatively large number ofcrop plants and weeds were placed in sandy loam ground and covered withsoil.

Some of the pots were treated immediately as described under 1., thoseremaining were placed in the greenhouse until the plants had developedtwo to three true leaves and were then sprayed with various dosages ofthe substances according to the invention as described under 2.

Four to five weeks after application, with the plants remaining in thegreenhouse, visual scoring revealed that the compounds according to theinvention did not cause any damage to dicotyledonous crops, such as, forexample, soya, cotton, rape, sugar beet and potatoes when applied bothas a pre-emergence and post-emergence treatment, even at high dosages ofactive substance. Furthermore, Gramineae crops such as, for example,barley, wheat, rye, sorghum millets, maize or rice, were also unaffectedby some of the substances. Thus, the compounds of the formula I exhibithigh selectivity on application for controlling undersired plant growthin agricultural crops.

                  TABLE 9                                                         ______________________________________                                        Pre-emergence action of the compounds according                               to the invention                                                                     Dosage in                                                              Ex. No.                                                                              kg of     herbicidal action                                            No.    a.i./ha   SIA    CRS  STM  AS   ECG   LOM                              ______________________________________                                        2      0.6       5      5    5    1    4     3                                3      0.6       5      5    5    2    5     2                                4      0.6       5      5    5    1    3     2                                71     0.6       5      5    3    3    4     4                                74     0.6       5      5    4    1    3     1                                84     0.6       5      5    5    1    3     1                                ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        Post-emergence action of the compounds                                        according to the invention                                                           Dosage in                                                              Ex. No.                                                                              kg of     herbicidal action                                            No.    a.i./ha   SIA    CRS  STM  AS   ECG   LOM                              ______________________________________                                        2      0.6       5      5    5    1    4     1                                3      0.6       5      5    5    1    4     2                                4      0.6       5      4    4    1    4     2                                71     0.6       5      4    4    3    4     3                                74     0.6       5      5    5    1    3     2                                84     0.6       5      5    5    0    5     3                                ______________________________________                                         Abbreviations:                                                                SIA = Sinapis alba-                                                           CRS = Chrysanthemum segetum-                                                  STM = Stellaria media-                                                        AS = Avena sativa-                                                            ECG = Echinochloa crus-galli-                                                 LOM = Lolium multiflorum-                                                     a.i. = active substance                                                  

We claim:
 1. A compound of formula I or a salt thereof ##STR21## whereR¹ is (C₂ -C₈)alkenyl;(C₂ -C₈)alkynyl; (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl or(C₂ -C₈)alkynyl, each of which is monosubstituted or polysubstituted bychloro or monosubstituted or disubstituted by (C₁ -C₆)alkoxy, (C₂-C₆)alkenyloxy, (C₂ -C₆)alkynyloxy, (C₁ -C₆)alkylthio, (C₁-C₆)alkylsulfinyl, (C₁ -C₆)alkysulfonyl, (C₁ -C₆)alkoxycarbonyl, NO₂, CNor by phenyl; (C₃ -C₈)cycloalkyl which can be monosubstituted orpolysubstituted by halogen or monosubstituted or disubstituted by (C₁-C₄)alkoxy or (C₁ -C₄)alkylthio; (C₅ -C₈)cycloalkenyl, cyclopropylmethylor epoxypropyl; furfuryl, tetrahydrofurfuryl or phenoxy-(C₁ -C₄)alkyl,each of which can be substituted by halogen, (C₁ -C₄)alkyl or (C₁-C₄)alkoxy; or phenyl which can be monosubstituted or polysubstituted byhalogen, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, NO₂, CF₃, CN or OCHF₂ ; or inthe event that R² is (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl orphenoxy, each of which can be substituted as indicated below, or R² is(C₁ -C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl, and further n≠0, then R¹can also be (C₁ -C₈)alkyl; R² is, each independently of any other R₂when n>1, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl,phenoxy, (C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio, (C₁ -C₄)alkoxycarbonyl, (C₂-C₄)alkenyloxycarbonyl or (C₂ -C₄)alkynyloxycarbonyl, each of which canbe monosubstituted or polysubstituted by halogen or monosubstituted ordisubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio; or is halogen,NO₂, (C₁ -C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl; n is 0, 1, 2 or 3;Y is O or S; R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₃-C₈)-alkynyl or (C₁ -C₄)alkoxy; R⁴ is a heterocyclic radical of formula##STR22## R⁵ and R⁶, independently of one another, are hydrogen orhalogen; (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy or (C₁ -C₆)alkylthio, each ofwhich can be monosubstituted or polysubstituted by halogen ormonosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio;or are a radical of the formula --NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃-C₆)cycloalkyl, (C₃ -C₅)alkenyl, (C₂ -C₅)alkynyl, (C₃ -C₅)alkenyloxy or(C₃ -C₅)alkynyloxy; R⁷ is hydrogen or (C₁ -C₄)alkyl; and R¹² and R¹³,independently of one another, are hydrogen, (C₁ -C₄)alkyl, (C₂-C₄)alkenyl or (C₃ -C₄)alkynyl.
 2. A compound of formula I or a saltthereof ##STR23## where R¹ is (C₂ -C₈)alkenyl;(C₂ -C₈)alkynyl; (C₁-C₈)alkyl, (C₂ -C₈)alkenyl or (C₂ -C₈)alkynyl, each of which ismonosubstituted or disubstituted by (C₁ -C₆)alkoxy, (C₂ -C₆)alkenyloxy,(C₂ -C₆)alkynyloxy, (C₁ -C₆)alkylthio, (C₁ -C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁ -C₆)alkoxycarbonyl, NO₂, CN or by phenyl; (C₃-C₈)cycloalkyl which can be monosubstituted or polysubstituted byhalogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁-C₄)alkylthio; (C₅ -C₈)cycloalkenyl, cyclopropylmethyl or epoxypropyl;furfuryl, tetrahydrofurfuryl or phenoxy-(C₁ -C₄)alkyl, each of which canbe substituted by halogen, (C₁ -C₄)alkyl or (C₁ -C₄)alkoxy; or phenylwhich can be monosubstituted or polysubstituted by halogen, (C₁-C₄)alkyl, (C₁ -C₄)alkoxy, NO₂, CF₃, CN or OCHF₂ ; or in the event thatR² is (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl or phenoxy, each of whichcan be substituted as indicated below, or R² is (C₁ -C₄)alkylsulfonyl or(C₁ -C₄)alkylsulfinyl, and further n≠0, then R¹ can also be (C₁-C₈)alkyl; R² is, each independently of any other R₂ when n>1, (C₁-C₈)alkyl, (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl, phenoxy, (C₁-C₄)alkoxy, (C₁ -C₄)alkylthio, (C₁ -C₄)alkoxycarbonyl, (C₂-C₄)alkenyloxycarbonyl or (C₂ -C₄)alkynyloxycarbonyl, each of which canbe monosubstituted or polysubstituted by halogen or monosubstituted ordisubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio; or is halogen,NO₂, (C₁ -C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl; n is 0, 1, 2 or 3;Y is O or S; R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₃-C₈)-alkynyl or (C₁ -C₄)alkoxy; R⁴ is a heterocyclic radical of formula##STR24## R⁵ and R⁶, independently of one another, are hydrogen orhalogen; (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy or (C₁ -C₆)alkylthio, each ofwhich can be monosubstituted or polysubstituted by halogen ormonosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio;or are a radical of the formula --NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃-C₆)cycloalkyl, (C₃ -C₅)alkenyl, (C₂ -C₄)alkynyl, (C₃ -C₅)alkenyloxy or(C₃ -C₅)alkynyloxy; R⁷ is hydrogen or (C₁ -C₄)alkyl; and R¹² and R¹³,independently of one another, are hydrogen, (C₁ -C₄)alkyl, (C₂-C₄)alkenyl or (C₃ -C₄)alkynyl.
 3. A compound of formula I or a saltthereof ##STR25## where R¹ is (C₂ -C₈)alkenyl;(C₂ -C₈)alkynyl; (C₁-C₈)alkyl, (C₂ -C₈)alkenyl or (C₂ -C₈)alkynyl, each of which ismonosubstituted or polysubstituted by chloro or bromo or monosubstitutedor disubstituted by (C₁ -C₆)alkoxy, (C₂ -C₆)alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁ -C₆)alkylthio, (C₁ -C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁ -C₆)alkoxycarbonyl, NO₂, CN or by phenyl; (C₃-C₈)cycloalkyl which can be monosubstituted or polysubstituted byhalogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁-C₄)alkylthio; (C₅ -C₈)cycloalkenyl, cyclopropylmethyl or epoxypropyl;furfuryl, tetrahydrofurfuryl or phenoxy-(C₁ -C₄)alkyl, each of which canbe substituted by halogen, (C₁ -C₄)alkyl or (C₁ -C₄)alkoxy; or phenylwhich can be monosubstituted or polysubstituted by halogen, (C₁-C₄)alkyl, (C₁ -C₄)alkoxy, NO₂, CF₃, CN or OCHF₂ ; or in the event thatR² is (C₂ -C₈)alkenyl, (C₂ -C₈)-alkynyl, phenyl or phenoxy, each ofwhich can be substituted as indicated below, or R² is (C₁-C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl, and further n≠0, then R¹ canalso be (C₁ -C₈)alkyl; R² is, each independently of any other R₂ whenn>1, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₂ -C₈)alkynyl, phenyl, phenoxy,(C₁ -C₄)alkoxy, (C₁ -C₄)alkylthio, (C₁ -C₄)-alkoxycarbonyl, (C₂-C₄)alkenyloxycarbonyl or (C₂ -C₄)-alkynyloxycarbonyl, each of which canbe monosubstituted or polysubstituted by halogen or monosubstituted ordisubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio; or is halogen,NO₂, (C₁ -C₄)alkylsulfonyl or (C₁ -C₄)alkylsulfinyl; n is 0, 1, 2 or 3;Y is O or S; R³ is hydrogen, (C₁ -C₈)alkyl, (C₂ -C₈)alkenyl, (C₃-C₈)-alkynyl or (C₁ -C₄)alkoxy; R⁴ is a heterocyclic radical of formula##STR26## R⁵ and R⁶, independently of one another, are hydrogen orhalogen; (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy or (C₁ -C₆)alkylthio, each ofwhich can be monosubstituted or polysubstituted by halogen ormonosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio;or are a radical of the formula --NR¹² R¹³, --OCHR⁷ --CO₂ R¹², (C₃-C₆)cycloalkyl, (C₃ -C₅)alkenyl, (C₂ -C₄)alkynyl, (C₃ -C₅)alkenyloxy or(C₃ -C₅)alkynyloxy; R⁷ is hydrogen or (C₁ -C₄)alkyl; and R¹² and R¹³,independently of one another, are hydrogen, (C₁ -C₄)alkyl, (C₂-C₄)alkenyl or (C₃ -C₄)alkynyl.
 4. A compound of the formula I of claim3 or a salt thereof, where R¹ is(C₁ -C₄)alkyl, (C₂ -C₅)alkenyl or (C₂-C₄)alkynyl, each of which is monosubstituted or polysubstituted bychloro or bromo or monosubstituted or disubstituted by (C₁ -C₆)alkoxy,(C₂ -C₆)alkenyloxy, (C₂ -C₆)-alkynyloxy, (C₁ -C₆)alkylthio, (C₁-C₆)alkylsulfinyl, (C₁ -C₆)alkylsulfonyl, (C₁ -C₆)alkoxycarbonyl, NO₂,CN or by phenyl, or (C₂ -C₅)alkenyl or (C₂ -C₄)alkynyl or, in the eventthat n=1 and R² is (C₂ -C₈)alkenyl or (C₂ -C₈)alkynyl, then R¹ can alsobe (C₁ -C₄)alkyl; R² is (C₁ -C₄)alkyl, (C₂ -C₅)alkenyl, (C₂ -C₄)alkynyl,(C₁ -C₄)alkoxycarbonyl, phenyl, phenoxy, (C₁ -C₄)alkoxy, (C₁-C₄)alkylthio, each of which can be monosubstituted or polysubstitued byhalogen or monosubstituted or disubstituted by (C₁ -C₄)alkoxy or (C₁-C₄)alkythio, or is halogen; n is 0, 1 or 2; Y is O; R³ is hydrogen, (C₁-C₄)alkyl or (C₃ -C₄)alkenyl; R⁴ is a heterocyclic radical of theformula ##STR27## R⁵ and R⁶ independently of one another are halogen, or(C₁ -C₄)alkyl, (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio, each of which can bemonosubstituted or poly substituted by halogen or monosubstituted ordisubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio.
 5. A compound ofthe formula I of claim 3 or a salt thereof, where R¹ is (C₁ -C₄)alkyl,(C₂ -C₅)alkenyl, or (C₂ -C₄)alkynyl, each of which is monosubstituted orpolysubstituted by chloro or bromo or monosubstituted or disubstitutedby (C₁ -C₆)alkoxy, (C₂ -C₆)alkenyloxy, (C₂ -C₆)-alkynyloxy, (C₁-C₆)alkylthio, (C₁ -C₆)alkylsulfinyl, (C₁ -C₆)alkylsulfonyl, (C₁-C₆)alkoxycarbonyl, NO₂, CN or by phenyl, or(C₂ -C₅)alkenyl or (C₂-C₄)alkynyl; R² is (C₁ -C₄)alkyl, (C₂ -C₅)alkenyl, (C₁-C₄)alkoxycarbonyl, (C₁ -C₄)alkoxy or (C₁ -C₄)alkylthio, each of whichcan be monosubstituted or polysubstituted by halogen or monosubstitutedor disubstituted by (C₁ -C₄)alkoxy or (C₁ -C₄)alkythio), or is fluorineor chlorine, n=0 or 1, R³ is hydrogen or methyl, R⁴ is a heterocyclicradical of the formula ##STR28## and R⁵ and R⁶ independently of oneanother are chlorine, bromine, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, OCHF₂,OCH₂ CF₃ or CF₃.
 6. A herbicidal composition containing an effectiveherbicidal amount of one or more compounds of the formula I or saltsthereof as claimed in claim 3 and inert auxilaries.
 7. A plantgrowth-regulating composition containing an effective plant-growthregulating amount of one or more compounds of the formula I or saltsthereof as claimed in claim 3 and inert auxiliaries.
 8. A method ofcontrolling weed plants, which comprises applying an effective amount ofone or more compounds of the formula I or salts thereof, as claimed inclaim 3, to these weed plants or the soil used for agriculture orindustry.
 9. A method of regulating the growth of crop plants whichcomprises applying an effective amount of one or more compounds of theformula I or salts thereof, as claimed in claim 3, to these crop plantsor the cropped area. 10.1-[2-(2-chloroethoxy)phenoxysulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea.11.3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea.12.3-(4,6-dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)-phenoxysulfonyl]urea.13. A compound of formula I, as claimed in claim 3, wherein R¹ is CH₂CH₂ OCH₃, R³ is H, R⁴ is ##STR29## R⁵ is CH₃, R⁶ is CH₃, n is 0 and Y isO.
 14. A compound of formula I, as claimed in claim 3, whereinR¹ is CH₂CH═CH₂, R³ is H, R⁴ is ##STR30## R⁵ is CH₃, R⁶ is CH₃, n is 0 and Y isO.
 15. A compound of formula I, as claimed in claim 3, wherein R¹ is CH₂CH═CH₂, R³ is H, R⁴ is ##STR31## R⁵ is OCH₃, R⁶ is CH₃, n is 0 and Y isO.
 16. A compound of formula I, as claimed in claim 3, wherein R¹ is CH₂CH═CH₂, R³ is H, R⁴ is ##STR32## R⁵ is OCH₃, R⁶ is OCH₃, n is 0 and Y isO.